The crystal structures of three (N-phenylthioureidoalkyl- and -aryl)phosphonates, i.e. diphenyl [(3-phenylthioureido)phenylpropyl]phosphonate, diphenyl [1-(3-phenylthioureido)benzyl]phosphonate and diphenyl [2,2-dimethyl-1-(3-phenylthioureido)propyl]phosphonate, have been determined by X-ray diffraction. The conformations of the title molecules, the geometry of the thioureide fragments and molecular packing arrangements are analyzed and compared with literature data.
Supporting information
CCDC references: 218518; 218519; 218520
For all compounds, data collection: MSC/AFC Diffractometer Control Software (1989a); cell refinement: MSC/AFC Diffractometer Control Software (1989a); data reduction: TEXSAN (1989b); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1998); software used to prepare material for publication: PARST97 (Nardelli, 1996).
(I) diphenyl [(3-phenylthioureido)phenylpropyl]phosphonate
top
Crystal data top
C28H27N2O3PS | Z = 2 |
Mr = 502.55 | F(000) = 528 |
Triclinic, P1 | Dx = 1.259 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.54178 Å |
a = 9.951 (1) Å | Cell parameters from 25 reflections |
b = 12.201 (1) Å | θ = 38.2–39.9° |
c = 11.844 (1) Å | µ = 1.91 mm−1 |
α = 100.40 (1)° | T = 293 K |
β = 102.90 (1)° | Prism, colourless |
γ = 102.90 (1)° | 0.50 × 0.30 × 0.20 mm |
V = 1325.6 (2) Å3 | |
Data collection top
AFC5S Rigaku diffractometer | 3089 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.030 |
Graphite monochromator | θmax = 67.5°, θmin = 3.8° |
ω scans | h = −11→11 |
Absorption correction: analytical (De Meulenaer & Tompa, 1965) | k = −14→14 |
Tmin = 0.448, Tmax = 0.701 | l = −11→14 |
4878 measured reflections | 3 standard reflections every 150 reflections |
4637 independent reflections | intensity decay: <2% |
Refinement top
Refinement on F2 | Secondary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.041 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.119 | w = 1/[σ2(Fo2) + (0.0663P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.94 | (Δ/σ)max < 0.001 |
4637 reflections | Δρmax = 0.21 e Å−3 |
325 parameters | Δρmin = −0.28 e Å−3 |
8 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0146 (7) |
Crystal data top
C28H27N2O3PS | γ = 102.90 (1)° |
Mr = 502.55 | V = 1325.6 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.951 (1) Å | Cu Kα radiation |
b = 12.201 (1) Å | µ = 1.91 mm−1 |
c = 11.844 (1) Å | T = 293 K |
α = 100.40 (1)° | 0.50 × 0.30 × 0.20 mm |
β = 102.90 (1)° | |
Data collection top
AFC5S Rigaku diffractometer | 3089 reflections with I > 2σ(I) |
Absorption correction: analytical (De Meulenaer & Tompa, 1965) | Rint = 0.030 |
Tmin = 0.448, Tmax = 0.701 | 3 standard reflections every 150 reflections |
4878 measured reflections | intensity decay: <2% |
4637 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.041 | 8 restraints |
wR(F2) = 0.119 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.94 | Δρmax = 0.21 e Å−3 |
4637 reflections | Δρmin = −0.28 e Å−3 |
325 parameters | |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 0.44040 (7) | 0.31491 (6) | 0.19540 (5) | 0.0739 (2) | |
C1 | 0.2730 (2) | 0.23518 (19) | 0.17094 (18) | 0.0530 (5) | |
N1 | 0.2123 (2) | 0.21260 (18) | 0.25830 (16) | 0.0604 (5) | |
H1 | 0.137 (2) | 0.1608 (19) | 0.235 (2) | 0.071 (8)* | |
N2 | 0.1818 (2) | 0.18510 (16) | 0.05978 (15) | 0.0554 (5) | |
H2 | 0.096 (2) | 0.1402 (19) | 0.056 (2) | 0.068 (8)* | |
C2 | 0.2245 (2) | 0.18120 (19) | −0.05049 (18) | 0.0552 (6) | |
H201 | 0.3276 | 0.2191 | −0.0288 | 0.066* | |
C3 | 0.1484 (3) | 0.24601 (19) | −0.1320 (2) | 0.0646 (6) | |
H301 | 0.1768 | 0.2368 | −0.2056 | 0.078* | |
H302 | 0.0456 | 0.2123 | −0.1520 | 0.078* | |
C4 | 0.1840 (3) | 0.3743 (2) | −0.0734 (2) | 0.0838 (9) | |
H401 | 0.1469 | 0.3833 | −0.0042 | 0.101* | |
H402 | 0.2874 | 0.4058 | −0.0457 | 0.101* | |
C51 | 0.1232 (3) | 0.4429 (2) | −0.1559 (2) | 0.0686 (7) | |
C52 | −0.0046 (3) | 0.4682 (2) | −0.1559 (2) | 0.0789 (8) | |
H52 | −0.0562 | 0.4412 | −0.1053 | 0.095* | |
C53 | −0.0573 (4) | 0.5328 (3) | −0.2296 (3) | 0.0950 (10) | |
H53 | −0.1447 | 0.5479 | −0.2290 | 0.114* | |
C54 | 0.0162 (4) | 0.5749 (3) | −0.3031 (3) | 0.1012 (10) | |
H54 | −0.0186 | 0.6206 | −0.3510 | 0.121* | |
C55 | 0.1432 (4) | 0.5489 (3) | −0.3058 (3) | 0.1078 (11) | |
H55 | 0.1931 | 0.5745 | −0.3580 | 0.129* | |
C56 | 0.1965 (3) | 0.4849 (3) | −0.2311 (3) | 0.0896 (9) | |
H56 | 0.2839 | 0.4699 | −0.2318 | 0.107* | |
P1 | 0.19730 (7) | 0.03069 (5) | −0.11821 (5) | 0.0559 (2) | |
O1 | 0.05416 (16) | −0.04412 (13) | −0.13141 (13) | 0.0615 (4) | |
O2 | 0.23898 (18) | 0.03783 (13) | −0.23782 (14) | 0.0694 (5) | |
O3 | 0.32302 (17) | −0.00571 (15) | −0.04221 (16) | 0.0721 (5) | |
C11 | 0.2849 (2) | 0.2468 (2) | 0.38339 (19) | 0.0574 (6) | |
C12 | 0.3023 (3) | 0.1639 (2) | 0.4444 (2) | 0.0766 (7) | |
H12 | 0.2708 | 0.0859 | 0.4046 | 0.092* | |
C13 | 0.3681 (3) | 0.1975 (3) | 0.5673 (3) | 0.0926 (9) | |
H13 | 0.3817 | 0.1418 | 0.6097 | 0.111* | |
C14 | 0.4121 (3) | 0.3114 (3) | 0.6245 (2) | 0.0910 (9) | |
H14 | 0.4547 | 0.3334 | 0.7065 | 0.109* | |
C15 | 0.3947 (3) | 0.3942 (3) | 0.5634 (2) | 0.0851 (9) | |
H15 | 0.4266 | 0.4721 | 0.6036 | 0.102* | |
C16 | 0.3301 (3) | 0.3627 (2) | 0.4426 (2) | 0.0683 (7) | |
H16 | 0.3168 | 0.4189 | 0.4010 | 0.082* | |
C21 | 0.2116 (3) | −0.0610 (2) | −0.33190 (19) | 0.0593 (6) | |
C22 | 0.0807 (3) | −0.0978 (3) | −0.4139 (2) | 0.0804 (8) | |
H22 | 0.0098 | −0.0610 | −0.4059 | 0.096* | |
C23 | 0.0554 (4) | −0.1902 (3) | −0.5085 (3) | 0.1042 (11) | |
H23 | −0.0340 | −0.2171 | −0.5643 | 0.125* | |
C24 | 0.1586 (5) | −0.2423 (3) | −0.5214 (3) | 0.1074 (12) | |
H24 | 0.1407 | −0.3037 | −0.5869 | 0.129* | |
C25 | 0.2905 (5) | −0.2055 (3) | −0.4385 (3) | 0.1025 (11) | |
H25 | 0.3610 | −0.2426 | −0.4472 | 0.123* | |
C26 | 0.3175 (3) | −0.1128 (3) | −0.3422 (3) | 0.0806 (8) | |
H26 | 0.4063 | −0.0865 | −0.2856 | 0.097* | |
C31 | 0.3108 (2) | −0.08783 (19) | 0.0249 (2) | 0.0614 (6) | |
C32 | 0.3310 (4) | −0.1936 (2) | −0.0180 (3) | 0.1039 (11) | |
H32 | 0.3452 | −0.2120 | −0.0934 | 0.125* | |
C33 | 0.3300 (4) | −0.2724 (3) | 0.0526 (3) | 0.1257 (14) | |
H33 | 0.3432 | −0.3443 | 0.0245 | 0.151* | |
C34 | 0.3095 (3) | −0.2449 (3) | 0.1646 (3) | 0.1040 (11) | |
H34 | 0.3084 | −0.2985 | 0.2115 | 0.125* | |
C35 | 0.2907 (4) | −0.1382 (3) | 0.2071 (3) | 0.1187 (12) | |
H35 | 0.2771 | −0.1195 | 0.2826 | 0.142* | |
C36 | 0.2923 (4) | −0.0592 (3) | 0.1371 (2) | 0.1049 (11) | |
H36 | 0.2809 | 0.0133 | 0.1658 | 0.126* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0622 (4) | 0.0842 (5) | 0.0536 (4) | −0.0046 (3) | 0.0118 (3) | −0.0013 (3) |
C1 | 0.0558 (13) | 0.0537 (12) | 0.0438 (11) | 0.0110 (10) | 0.0114 (10) | 0.0051 (10) |
N1 | 0.0600 (13) | 0.0648 (13) | 0.0423 (10) | 0.0005 (10) | 0.0081 (9) | 0.0061 (9) |
N2 | 0.0550 (12) | 0.0595 (12) | 0.0406 (10) | 0.0043 (10) | 0.0084 (9) | 0.0049 (8) |
C2 | 0.0623 (14) | 0.0537 (13) | 0.0421 (11) | 0.0075 (11) | 0.0109 (10) | 0.0076 (10) |
C3 | 0.0807 (17) | 0.0584 (14) | 0.0485 (13) | 0.0154 (13) | 0.0110 (12) | 0.0104 (11) |
C4 | 0.122 (2) | 0.0632 (16) | 0.0594 (16) | 0.0296 (16) | 0.0113 (15) | 0.0098 (13) |
C51 | 0.087 (2) | 0.0559 (14) | 0.0590 (15) | 0.0195 (14) | 0.0158 (14) | 0.0108 (12) |
C52 | 0.089 (2) | 0.088 (2) | 0.0609 (16) | 0.0228 (17) | 0.0253 (14) | 0.0181 (15) |
C53 | 0.105 (2) | 0.114 (3) | 0.079 (2) | 0.053 (2) | 0.0272 (18) | 0.0252 (19) |
C54 | 0.129 (3) | 0.100 (2) | 0.097 (2) | 0.053 (2) | 0.033 (2) | 0.047 (2) |
C55 | 0.131 (3) | 0.112 (3) | 0.111 (3) | 0.039 (2) | 0.059 (2) | 0.064 (2) |
C56 | 0.095 (2) | 0.099 (2) | 0.098 (2) | 0.0425 (19) | 0.0428 (18) | 0.0421 (19) |
P1 | 0.0611 (4) | 0.0535 (3) | 0.0468 (3) | 0.0071 (3) | 0.0150 (3) | 0.0073 (3) |
O1 | 0.0564 (10) | 0.0610 (9) | 0.0529 (9) | −0.0003 (8) | 0.0107 (7) | 0.0050 (7) |
O2 | 0.0926 (13) | 0.0573 (9) | 0.0559 (9) | 0.0088 (9) | 0.0330 (9) | 0.0065 (8) |
O3 | 0.0601 (10) | 0.0740 (11) | 0.0838 (12) | 0.0153 (9) | 0.0156 (9) | 0.0326 (10) |
C11 | 0.0588 (14) | 0.0667 (14) | 0.0416 (12) | 0.0119 (11) | 0.0115 (10) | 0.0095 (11) |
C12 | 0.088 (2) | 0.0750 (17) | 0.0690 (17) | 0.0220 (15) | 0.0209 (14) | 0.0253 (14) |
C13 | 0.099 (2) | 0.124 (3) | 0.0696 (19) | 0.037 (2) | 0.0234 (16) | 0.051 (2) |
C14 | 0.082 (2) | 0.131 (3) | 0.0495 (16) | 0.020 (2) | 0.0088 (14) | 0.0183 (18) |
C15 | 0.092 (2) | 0.092 (2) | 0.0517 (15) | 0.0073 (17) | 0.0134 (14) | −0.0020 (15) |
C16 | 0.0815 (18) | 0.0652 (15) | 0.0479 (13) | 0.0128 (13) | 0.0096 (12) | 0.0076 (12) |
C21 | 0.0729 (16) | 0.0600 (14) | 0.0460 (12) | 0.0154 (12) | 0.0222 (12) | 0.0114 (11) |
C22 | 0.086 (2) | 0.098 (2) | 0.0550 (15) | 0.0300 (17) | 0.0132 (14) | 0.0152 (15) |
C23 | 0.121 (3) | 0.107 (3) | 0.0575 (18) | 0.011 (2) | 0.0061 (18) | 0.0022 (17) |
C24 | 0.168 (4) | 0.081 (2) | 0.065 (2) | 0.016 (2) | 0.047 (2) | −0.0013 (16) |
C25 | 0.149 (3) | 0.088 (2) | 0.105 (3) | 0.058 (2) | 0.075 (3) | 0.028 (2) |
C26 | 0.082 (2) | 0.092 (2) | 0.0732 (18) | 0.0307 (17) | 0.0267 (15) | 0.0180 (16) |
C31 | 0.0552 (14) | 0.0591 (14) | 0.0671 (15) | 0.0148 (11) | 0.0114 (12) | 0.0166 (12) |
C32 | 0.152 (3) | 0.073 (2) | 0.089 (2) | 0.038 (2) | 0.036 (2) | 0.0130 (17) |
C33 | 0.175 (4) | 0.065 (2) | 0.134 (3) | 0.038 (2) | 0.028 (3) | 0.030 (2) |
C34 | 0.089 (2) | 0.096 (3) | 0.121 (3) | 0.0116 (19) | 0.005 (2) | 0.057 (2) |
C35 | 0.155 (4) | 0.136 (3) | 0.096 (3) | 0.065 (3) | 0.046 (2) | 0.059 (3) |
C36 | 0.165 (3) | 0.092 (2) | 0.082 (2) | 0.064 (2) | 0.045 (2) | 0.0317 (18) |
Geometric parameters (Å, º) top
S1—C1 | 1.663 (2) | C11—C16 | 1.382 (3) |
C1—N1 | 1.349 (3) | C12—C13 | 1.398 (4) |
C1—N2 | 1.363 (3) | C12—H12 | 0.9300 |
N1—C11 | 1.434 (3) | C13—C14 | 1.356 (4) |
N1—H1 | 0.821 (19) | C13—H13 | 0.9300 |
N2—C2 | 1.457 (3) | C14—C15 | 1.364 (4) |
N2—H2 | 0.891 (19) | C14—H14 | 0.9300 |
C2—C3 | 1.532 (3) | C15—C16 | 1.374 (3) |
C2—P1 | 1.799 (2) | C15—H15 | 0.9300 |
C2—H201 | 0.9800 | C16—H16 | 0.9300 |
C3—C4 | 1.519 (3) | C21—C26 | 1.362 (3) |
C3—H301 | 0.9700 | C21—C22 | 1.363 (3) |
C3—H302 | 0.9700 | C22—C23 | 1.371 (4) |
C4—C51 | 1.510 (3) | C22—H22 | 0.9300 |
C4—H401 | 0.9700 | C23—C24 | 1.344 (5) |
C4—H402 | 0.9700 | C23—H23 | 0.9300 |
C51—C56 | 1.369 (4) | C24—C25 | 1.374 (5) |
C51—C52 | 1.374 (4) | C24—H24 | 0.9300 |
C52—C53 | 1.373 (4) | C25—C26 | 1.383 (4) |
C52—H52 | 0.9300 | C25—H25 | 0.9300 |
C53—C54 | 1.354 (4) | C26—H26 | 0.9300 |
C53—H53 | 0.9300 | C31—C36 | 1.3750 (18) |
C54—C55 | 1.375 (4) | C31—C32 | 1.374 (4) |
C54—H54 | 0.9300 | C32—C33 | 1.383 (5) |
C55—C56 | 1.378 (4) | C32—H32 | 0.9300 |
C55—H55 | 0.9300 | C33—C34 | 1.380 (5) |
C56—H56 | 0.9300 | C33—H33 | 0.9300 |
P1—O1 | 1.4680 (15) | C34—C35 | 1.378 (5) |
P1—O3 | 1.5691 (17) | C34—H34 | 0.9300 |
P1—O2 | 1.5740 (16) | C35—C36 | 1.380 (5) |
O2—C21 | 1.415 (3) | C35—H35 | 0.9300 |
O3—C31 | 1.388 (3) | C36—H36 | 0.9300 |
C11—C12 | 1.364 (3) | | |
| | | |
N1—C1—N2 | 112.47 (19) | C12—C11—N1 | 119.5 (2) |
N1—C1—S1 | 124.00 (17) | C16—C11—N1 | 120.0 (2) |
N2—C1—S1 | 123.53 (17) | C11—C12—C13 | 119.3 (3) |
C1—N1—C11 | 125.1 (2) | C11—C12—H12 | 120.3 |
C1—N1—H1 | 114.3 (17) | C13—C12—H12 | 120.3 |
C11—N1—H1 | 118.3 (17) | C14—C13—C12 | 119.8 (3) |
C1—N2—C2 | 124.18 (19) | C14—C13—H13 | 120.1 |
C1—N2—H2 | 116.4 (15) | C12—C13—H13 | 120.1 |
C2—N2—H2 | 118.2 (15) | C13—C14—C15 | 120.8 (3) |
N2—C2—C3 | 112.88 (19) | C13—C14—H14 | 119.6 |
N2—C2—P1 | 106.59 (14) | C15—C14—H14 | 119.6 |
C3—C2—P1 | 114.31 (15) | C14—C15—C16 | 120.1 (3) |
N2—C2—H201 | 107.6 | C14—C15—H15 | 120.0 |
C3—C2—H201 | 107.6 | C16—C15—H15 | 120.0 |
P1—C2—H201 | 107.6 | C15—C16—C11 | 119.6 (3) |
C4—C3—C2 | 111.93 (19) | C15—C16—H16 | 120.2 |
C4—C3—H301 | 109.2 | C11—C16—H16 | 120.2 |
C2—C3—H301 | 109.2 | C26—C21—C22 | 121.7 (2) |
C4—C3—H302 | 109.2 | C26—C21—O2 | 119.8 (2) |
C2—C3—H302 | 109.2 | C22—C21—O2 | 118.4 (2) |
H301—C3—H302 | 107.9 | C21—C22—C23 | 118.8 (3) |
C51—C4—C3 | 113.3 (2) | C21—C22—H22 | 120.6 |
C51—C4—H401 | 108.9 | C23—C22—H22 | 120.6 |
C3—C4—H401 | 108.9 | C24—C23—C22 | 120.6 (3) |
C51—C4—H402 | 108.9 | C24—C23—H23 | 119.7 |
C3—C4—H402 | 108.9 | C22—C23—H23 | 119.7 |
H401—C4—H402 | 107.7 | C23—C24—C25 | 120.6 (3) |
C56—C51—C52 | 117.8 (3) | C23—C24—H24 | 119.7 |
C56—C51—C4 | 120.7 (3) | C25—C24—H24 | 119.7 |
C52—C51—C4 | 121.5 (3) | C24—C25—C26 | 119.5 (3) |
C53—C52—C51 | 121.0 (3) | C24—C25—H25 | 120.2 |
C53—C52—H52 | 119.5 | C26—C25—H25 | 120.2 |
C51—C52—H52 | 119.5 | C21—C26—C25 | 118.7 (3) |
C54—C53—C52 | 121.0 (3) | C21—C26—H26 | 120.6 |
C54—C53—H53 | 119.5 | C25—C26—H26 | 120.6 |
C52—C53—H53 | 119.5 | C36—C31—C32 | 120.9 (2) |
C53—C54—C55 | 118.9 (3) | C36—C31—O3 | 120.1 (2) |
C53—C54—H54 | 120.6 | C32—C31—O3 | 118.7 (2) |
C55—C54—H54 | 120.6 | C31—C32—C33 | 118.9 (3) |
C54—C55—C56 | 120.0 (3) | C31—C32—H32 | 120.5 |
C54—C55—H55 | 120.0 | C33—C32—H32 | 120.5 |
C56—C55—H55 | 120.0 | C34—C33—C32 | 120.5 (3) |
C51—C56—C55 | 121.3 (3) | C34—C33—H33 | 119.7 |
C51—C56—H56 | 119.3 | C32—C33—H33 | 119.7 |
C55—C56—H56 | 119.3 | C35—C34—C33 | 120.0 (3) |
O1—P1—O3 | 114.03 (9) | C35—C34—H34 | 120.0 |
O1—P1—O2 | 115.74 (9) | C33—C34—H34 | 120.0 |
O3—P1—O2 | 103.91 (10) | C34—C35—C36 | 119.7 (3) |
O1—P1—C2 | 114.59 (10) | C34—C35—H35 | 120.1 |
O3—P1—C2 | 105.48 (10) | C36—C35—H35 | 120.1 |
O2—P1—C2 | 101.63 (9) | C31—C36—C35 | 119.9 (3) |
C21—O2—P1 | 122.72 (14) | C31—C36—H36 | 120.0 |
C31—O3—P1 | 126.81 (15) | C35—C36—H36 | 120.0 |
C12—C11—C16 | 120.4 (2) | | |
| | | |
N2—C1—N1—C11 | 175.4 (2) | C1—N1—C11—C12 | −115.1 (3) |
S1—C1—N1—C11 | −4.5 (4) | C1—N1—C11—C16 | 68.2 (3) |
N1—C1—N2—C2 | −170.9 (2) | C16—C11—C12—C13 | −0.8 (4) |
S1—C1—N2—C2 | 9.0 (3) | N1—C11—C12—C13 | −177.5 (2) |
C1—N2—C2—C3 | −117.7 (2) | C11—C12—C13—C14 | 0.8 (5) |
C1—N2—C2—P1 | 116.0 (2) | C12—C13—C14—C15 | −0.8 (5) |
N2—C2—C3—C4 | 62.1 (3) | C13—C14—C15—C16 | 0.9 (5) |
P1—C2—C3—C4 | −175.80 (19) | C14—C15—C16—C11 | −1.0 (4) |
C2—C3—C4—C51 | 174.0 (2) | C12—C11—C16—C15 | 0.9 (4) |
C3—C4—C51—C56 | −85.6 (3) | N1—C11—C16—C15 | 177.6 (2) |
C3—C4—C51—C52 | 96.3 (3) | P1—O2—C21—C26 | −97.4 (3) |
C56—C51—C52—C53 | 0.4 (4) | P1—O2—C21—C22 | 86.1 (3) |
C4—C51—C52—C53 | 178.6 (3) | C26—C21—C22—C23 | 0.6 (4) |
C51—C52—C53—C54 | −1.0 (5) | O2—C21—C22—C23 | 177.0 (2) |
C52—C53—C54—C55 | 2.0 (5) | C21—C22—C23—C24 | −1.2 (5) |
C53—C54—C55—C56 | −2.5 (6) | C22—C23—C24—C25 | 1.4 (6) |
C52—C51—C56—C55 | −1.0 (4) | C23—C24—C25—C26 | −1.1 (5) |
C4—C51—C56—C55 | −179.2 (3) | C22—C21—C26—C25 | −0.2 (4) |
C54—C55—C56—C51 | 2.1 (5) | O2—C21—C26—C25 | −176.6 (2) |
N2—C2—P1—O1 | 51.62 (18) | C24—C25—C26—C21 | 0.4 (5) |
C3—C2—P1—O1 | −73.82 (19) | P1—O3—C31—C36 | −80.9 (3) |
N2—C2—P1—O3 | −74.64 (16) | P1—O3—C31—C32 | 105.2 (3) |
C3—C2—P1—O3 | 159.92 (16) | C36—C31—C32—C33 | 1.2 (5) |
N2—C2—P1—O2 | 177.20 (14) | O3—C31—C32—C33 | 175.0 (3) |
C3—C2—P1—O2 | 51.76 (19) | C31—C32—C33—C34 | −0.2 (6) |
O1—P1—O2—C21 | −44.1 (2) | C32—C33—C34—C35 | −0.4 (6) |
O3—P1—O2—C21 | 81.70 (19) | C33—C34—C35—C36 | 0.1 (6) |
C2—P1—O2—C21 | −168.93 (19) | C32—C31—C36—C35 | −1.4 (5) |
O1—P1—O3—C31 | −9.8 (2) | O3—C31—C36—C35 | −175.2 (3) |
O2—P1—O3—C31 | −136.67 (18) | C34—C35—C36—C31 | 0.8 (6) |
C2—P1—O3—C31 | 116.82 (19) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.82 (2) | 2.06 (2) | 2.861 (2) | 163 (2) |
N2—H2···O1i | 0.89 (2) | 2.14 (2) | 2.967 (2) | 153 (2) |
Symmetry code: (i) −x, −y, −z. |
(II) diphenyl [1-(3-phenylthioureido)benzyl]phosphonate
top
Crystal data top
C26H23N2O3PS | Z = 2 |
Mr = 474.49 | F(000) = 496 |
Triclinic, P1 | Dx = 1.319 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.54178 Å |
a = 9.953 (1) Å | Cell parameters from 22 reflections |
b = 10.046 (1) Å | θ = 22.6–29.5° |
c = 12.701 (1) Å | µ = 2.09 mm−1 |
α = 96.66 (1)° | T = 293 K |
β = 104.45 (1)° | Plate, colourless |
γ = 99.84 (1)° | 0.2 × 0.2 × 0.1 mm |
V = 1194.8 (2) Å3 | |
Data collection top
AFC5S Rigaku diffractometer | 2147 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.019 |
Graphite monochromator | θmax = 67.5°, θmin = 3.6° |
ω scans | h = −11→11 |
Absorption correction: analytical (De Meulenaer & Tompa, 1965) | k = −11→12 |
Tmin = 0.675, Tmax = 0.836 | l = −15→15 |
4431 measured reflections | 3 standard reflections every 150 reflections |
4169 independent reflections | intensity decay: <2% |
Refinement top
Refinement on F2 | Secondary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.038 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.090 |
[1.00000exp(3.00(sinθ/λ)2)]/
[σ2(Fo2) + 0.0000*P + (0.029P)2]
where P = 0.33333Fo2 + 0.66667Fc2 |
S = 1.00 | (Δ/σ)max < 0.001 |
4169 reflections | Δρmax = 0.19 e Å−3 |
307 parameters | Δρmin = −0.23 e Å−3 |
8 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0060 (3) |
Crystal data top
C26H23N2O3PS | γ = 99.84 (1)° |
Mr = 474.49 | V = 1194.8 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.953 (1) Å | Cu Kα radiation |
b = 10.046 (1) Å | µ = 2.09 mm−1 |
c = 12.701 (1) Å | T = 293 K |
α = 96.66 (1)° | 0.2 × 0.2 × 0.1 mm |
β = 104.45 (1)° | |
Data collection top
AFC5S Rigaku diffractometer | 2147 reflections with I > 2σ(I) |
Absorption correction: analytical (De Meulenaer & Tompa, 1965) | Rint = 0.019 |
Tmin = 0.675, Tmax = 0.836 | 3 standard reflections every 150 reflections |
4431 measured reflections | intensity decay: <2% |
4169 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.038 | 8 restraints |
wR(F2) = 0.090 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | Δρmax = 0.19 e Å−3 |
4169 reflections | Δρmin = −0.23 e Å−3 |
307 parameters | |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 0.42318 (8) | 0.35393 (8) | 0.18474 (6) | 0.0552 (2) | |
C1 | 0.2577 (3) | 0.2655 (3) | 0.1562 (2) | 0.0434 (7) | |
N1 | 0.1930 (3) | 0.2320 (3) | 0.23379 (18) | 0.0532 (6) | |
H1 | 0.117 (3) | 0.170 (3) | 0.206 (2) | 0.086 (12)* | |
N2 | 0.1737 (3) | 0.2185 (3) | 0.05246 (18) | 0.0515 (6) | |
H2 | 0.096 (3) | 0.167 (3) | 0.046 (2) | 0.081 (12)* | |
C2 | 0.2215 (3) | 0.2261 (3) | −0.0465 (2) | 0.0479 (7) | |
H201 | 0.3243 | 0.2610 | −0.0216 | 0.057* | |
C41 | 0.1596 (3) | 0.3245 (3) | −0.1180 (2) | 0.0488 (7) | |
C42 | 0.2302 (4) | 0.3774 (3) | −0.1895 (2) | 0.0681 (9) | |
H42 | 0.3126 | 0.3491 | −0.1955 | 0.082* | |
C43 | 0.1817 (4) | 0.4708 (4) | −0.2518 (3) | 0.0806 (11) | |
H43 | 0.2311 | 0.5052 | −0.2994 | 0.097* | |
C44 | 0.0609 (4) | 0.5134 (4) | −0.2442 (3) | 0.0809 (11) | |
H44 | 0.0275 | 0.5765 | −0.2867 | 0.097* | |
C45 | −0.0106 (4) | 0.4630 (4) | −0.1739 (3) | 0.0956 (13) | |
H45 | −0.0925 | 0.4925 | −0.1679 | 0.115* | |
C46 | 0.0386 (3) | 0.3676 (4) | −0.1112 (3) | 0.0773 (10) | |
H46 | −0.0115 | 0.3328 | −0.0641 | 0.093* | |
P1 | 0.19360 (8) | 0.05058 (8) | −0.11229 (6) | 0.0506 (2) | |
O1 | 0.05553 (19) | −0.03446 (19) | −0.11845 (14) | 0.0566 (5) | |
O2 | 0.2266 (2) | 0.06605 (19) | −0.22583 (14) | 0.0612 (6) | |
O3 | 0.3242 (2) | −0.0014 (2) | −0.04599 (16) | 0.0637 (6) | |
C11 | 0.2629 (3) | 0.2483 (3) | 0.3487 (2) | 0.0521 (7) | |
C12 | 0.2855 (4) | 0.1331 (4) | 0.3931 (3) | 0.0753 (10) | |
H12 | 0.2592 | 0.0474 | 0.3486 | 0.090* | |
C13 | 0.3482 (4) | 0.1469 (5) | 0.5051 (3) | 0.1023 (15) | |
H13 | 0.3642 | 0.0697 | 0.5361 | 0.123* | |
C14 | 0.3869 (4) | 0.2723 (6) | 0.5703 (3) | 0.1088 (18) | |
H14 | 0.4284 | 0.2802 | 0.6456 | 0.131* | |
C15 | 0.3648 (4) | 0.3861 (5) | 0.5256 (3) | 0.0952 (13) | |
H15 | 0.3922 | 0.4718 | 0.5702 | 0.114* | |
C16 | 0.3015 (3) | 0.3744 (3) | 0.4136 (2) | 0.0693 (9) | |
H16 | 0.2854 | 0.4518 | 0.3829 | 0.083* | |
C21 | 0.2082 (3) | −0.0483 (3) | −0.3075 (2) | 0.0548 (8) | |
C22 | 0.0815 (4) | −0.0869 (4) | −0.3868 (3) | 0.0732 (10) | |
H22 | 0.0075 | −0.0426 | −0.3840 | 0.088* | |
C23 | 0.0654 (4) | −0.1934 (4) | −0.4717 (3) | 0.0915 (12) | |
H23 | −0.0199 | −0.2210 | −0.5267 | 0.110* | |
C24 | 0.1753 (5) | −0.2579 (4) | −0.4745 (3) | 0.0959 (13) | |
H24 | 0.1644 | −0.3291 | −0.5317 | 0.115* | |
C25 | 0.3000 (4) | −0.2188 (4) | −0.3944 (3) | 0.0837 (11) | |
H25 | 0.3738 | −0.2635 | −0.3972 | 0.100* | |
C26 | 0.3183 (3) | −0.1131 (3) | −0.3088 (2) | 0.0656 (9) | |
H26 | 0.4034 | −0.0867 | −0.2533 | 0.079* | |
C31 | 0.3225 (3) | −0.1048 (3) | 0.0186 (2) | 0.0526 (7) | |
C32 | 0.3441 (4) | −0.2300 (3) | −0.0224 (3) | 0.0755 (10) | |
H32 | 0.3502 | −0.2481 | −0.0944 | 0.091* | |
C33 | 0.3566 (4) | −0.3286 (3) | 0.0448 (2) | 0.0800 (11) | |
H33 | 0.3713 | −0.4133 | 0.0176 | 0.096* | |
C34 | 0.3475 (3) | −0.3036 (3) | 0.1515 (2) | 0.0736 (10) | |
H34 | 0.3556 | −0.3706 | 0.1962 | 0.088* | |
C35 | 0.3262 (5) | −0.1772 (3) | 0.1907 (3) | 0.1026 (14) | |
H35 | 0.3204 | −0.1591 | 0.2627 | 0.123* | |
C36 | 0.3132 (4) | −0.0769 (3) | 0.1250 (2) | 0.0889 (12) | |
H36 | 0.2984 | 0.0078 | 0.1521 | 0.107* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0522 (5) | 0.0564 (5) | 0.0503 (4) | 0.0032 (4) | 0.0088 (4) | 0.0050 (4) |
C1 | 0.0455 (17) | 0.0445 (16) | 0.0377 (14) | 0.0113 (13) | 0.0058 (12) | 0.0066 (12) |
N1 | 0.0537 (16) | 0.0625 (17) | 0.0371 (13) | 0.0002 (14) | 0.0104 (12) | 0.0054 (12) |
N2 | 0.0492 (16) | 0.0641 (17) | 0.0366 (13) | 0.0042 (14) | 0.0093 (12) | 0.0063 (12) |
C2 | 0.0482 (17) | 0.0558 (18) | 0.0387 (15) | 0.0091 (14) | 0.0113 (13) | 0.0077 (13) |
C41 | 0.0521 (18) | 0.0516 (18) | 0.0406 (15) | 0.0092 (15) | 0.0105 (13) | 0.0064 (13) |
C42 | 0.080 (2) | 0.072 (2) | 0.068 (2) | 0.0296 (19) | 0.0318 (18) | 0.0279 (19) |
C43 | 0.105 (3) | 0.080 (3) | 0.076 (2) | 0.030 (2) | 0.042 (2) | 0.037 (2) |
C44 | 0.090 (3) | 0.083 (3) | 0.073 (2) | 0.029 (2) | 0.014 (2) | 0.031 (2) |
C45 | 0.082 (3) | 0.118 (4) | 0.116 (3) | 0.052 (3) | 0.039 (2) | 0.064 (3) |
C46 | 0.071 (2) | 0.097 (3) | 0.083 (2) | 0.031 (2) | 0.0315 (19) | 0.047 (2) |
P1 | 0.0520 (5) | 0.0547 (5) | 0.0442 (4) | 0.0090 (4) | 0.0133 (4) | 0.0068 (4) |
O1 | 0.0473 (12) | 0.0625 (13) | 0.0517 (12) | −0.0036 (10) | 0.0121 (9) | 0.0023 (10) |
O2 | 0.0854 (15) | 0.0561 (13) | 0.0467 (11) | 0.0119 (11) | 0.0302 (11) | 0.0043 (10) |
O3 | 0.0494 (12) | 0.0654 (14) | 0.0813 (15) | 0.0161 (11) | 0.0154 (10) | 0.0314 (12) |
C11 | 0.0557 (18) | 0.062 (2) | 0.0370 (15) | 0.0095 (16) | 0.0124 (13) | 0.0078 (14) |
C12 | 0.098 (3) | 0.079 (2) | 0.062 (2) | 0.031 (2) | 0.030 (2) | 0.0263 (19) |
C13 | 0.109 (3) | 0.155 (5) | 0.071 (3) | 0.060 (3) | 0.035 (3) | 0.061 (3) |
C14 | 0.084 (3) | 0.200 (6) | 0.044 (2) | 0.034 (4) | 0.014 (2) | 0.028 (3) |
C15 | 0.095 (3) | 0.123 (4) | 0.049 (2) | −0.002 (3) | 0.015 (2) | −0.015 (2) |
C16 | 0.080 (2) | 0.072 (2) | 0.0486 (18) | 0.0083 (19) | 0.0137 (17) | 0.0002 (17) |
C21 | 0.067 (2) | 0.0546 (19) | 0.0465 (17) | 0.0156 (17) | 0.0210 (15) | 0.0068 (15) |
C22 | 0.067 (2) | 0.085 (3) | 0.066 (2) | 0.022 (2) | 0.0147 (18) | 0.005 (2) |
C23 | 0.089 (3) | 0.099 (3) | 0.065 (2) | 0.007 (2) | 0.000 (2) | −0.004 (2) |
C24 | 0.137 (4) | 0.080 (3) | 0.066 (2) | 0.029 (3) | 0.025 (3) | −0.008 (2) |
C25 | 0.109 (3) | 0.083 (3) | 0.078 (3) | 0.048 (2) | 0.039 (2) | 0.017 (2) |
C26 | 0.073 (2) | 0.073 (2) | 0.0565 (19) | 0.0268 (19) | 0.0201 (17) | 0.0126 (17) |
C31 | 0.0459 (17) | 0.0489 (19) | 0.0618 (19) | 0.0108 (14) | 0.0109 (14) | 0.0122 (15) |
C32 | 0.097 (3) | 0.060 (2) | 0.072 (2) | 0.025 (2) | 0.026 (2) | 0.0058 (19) |
C33 | 0.094 (3) | 0.050 (2) | 0.092 (3) | 0.0206 (19) | 0.016 (2) | 0.008 (2) |
C34 | 0.077 (2) | 0.060 (2) | 0.079 (2) | 0.0158 (19) | 0.008 (2) | 0.0211 (19) |
C35 | 0.173 (4) | 0.084 (3) | 0.068 (2) | 0.061 (3) | 0.036 (3) | 0.025 (2) |
C36 | 0.150 (4) | 0.064 (2) | 0.064 (2) | 0.053 (2) | 0.028 (2) | 0.0175 (19) |
Geometric parameters (Å, º) top
S1—C1 | 1.662 (3) | C13—C14 | 1.362 (5) |
C1—N1 | 1.349 (3) | C13—H13 | 0.9300 |
C1—N2 | 1.352 (3) | C14—C15 | 1.361 (5) |
N1—C11 | 1.429 (3) | C14—H14 | 0.9300 |
N1—H1 | 0.86 (2) | C15—C16 | 1.387 (4) |
N2—C2 | 1.456 (3) | C15—H15 | 0.9300 |
N2—H2 | 0.84 (2) | C16—H16 | 0.9300 |
C2—C41 | 1.522 (3) | C21—C22 | 1.365 (4) |
C2—P1 | 1.806 (3) | C21—C26 | 1.370 (4) |
C2—H201 | 0.9800 | C22—C23 | 1.386 (4) |
C41—C46 | 1.367 (4) | C22—H22 | 0.9300 |
C41—C42 | 1.380 (4) | C23—C24 | 1.369 (5) |
C42—C43 | 1.369 (4) | C23—H23 | 0.9300 |
C42—H42 | 0.9300 | C24—C25 | 1.356 (5) |
C43—C44 | 1.365 (4) | C24—H24 | 0.9300 |
C43—H43 | 0.9300 | C25—C26 | 1.382 (4) |
C44—C45 | 1.363 (4) | C25—H25 | 0.9300 |
C44—H44 | 0.9300 | C26—H26 | 0.9300 |
C45—C46 | 1.391 (4) | C31—C36 | 1.377 (4) |
C45—H45 | 0.9300 | C31—C32 | 1.377 (4) |
C46—H46 | 0.9300 | C32—C33 | 1.382 (4) |
P1—O1 | 1.4677 (19) | C32—H32 | 0.9300 |
P1—O3 | 1.5680 (19) | C33—C34 | 1.378 (4) |
P1—O2 | 1.5757 (18) | C33—H33 | 0.9300 |
O2—C21 | 1.410 (3) | C34—C35 | 1.380 (5) |
O3—C31 | 1.397 (3) | C34—H34 | 0.9300 |
C11—C16 | 1.365 (4) | C35—C36 | 1.383 (4) |
C11—C12 | 1.373 (4) | C35—H35 | 0.9300 |
C12—C13 | 1.383 (4) | C36—H36 | 0.9300 |
C12—H12 | 0.9300 | | |
| | | |
N1—C1—N2 | 112.7 (2) | C14—C13—H13 | 119.6 |
N1—C1—S1 | 123.7 (2) | C12—C13—H13 | 119.6 |
N2—C1—S1 | 123.5 (2) | C15—C14—C13 | 120.1 (4) |
C1—N1—C11 | 124.6 (2) | C15—C14—H14 | 119.9 |
C1—N1—H1 | 112 (2) | C13—C14—H14 | 119.9 |
C11—N1—H1 | 119 (2) | C14—C15—C16 | 120.0 (4) |
C1—N2—C2 | 124.2 (3) | C14—C15—H15 | 120.0 |
C1—N2—H2 | 117 (2) | C16—C15—H15 | 120.0 |
C2—N2—H2 | 118 (2) | C11—C16—C15 | 119.5 (3) |
N2—C2—C41 | 114.5 (2) | C11—C16—H16 | 120.2 |
N2—C2—P1 | 105.27 (19) | C15—C16—H16 | 120.2 |
C41—C2—P1 | 116.62 (17) | C22—C21—C26 | 121.9 (3) |
N2—C2—H201 | 106.6 | C22—C21—O2 | 118.2 (3) |
C41—C2—H201 | 106.6 | C26—C21—O2 | 119.8 (3) |
P1—C2—H201 | 106.6 | C21—C22—C23 | 118.7 (3) |
C46—C41—C42 | 118.0 (3) | C21—C22—H22 | 120.6 |
C46—C41—C2 | 122.4 (3) | C23—C22—H22 | 120.6 |
C42—C41—C2 | 119.5 (3) | C24—C23—C22 | 119.9 (3) |
C43—C42—C41 | 121.5 (3) | C24—C23—H23 | 120.0 |
C43—C42—H42 | 119.3 | C22—C23—H23 | 120.0 |
C41—C42—H42 | 119.3 | C25—C24—C23 | 120.5 (4) |
C44—C43—C42 | 120.1 (3) | C25—C24—H24 | 119.8 |
C44—C43—H43 | 120.0 | C23—C24—H24 | 119.8 |
C42—C43—H43 | 120.0 | C24—C25—C26 | 120.7 (4) |
C45—C44—C43 | 119.6 (3) | C24—C25—H25 | 119.7 |
C45—C44—H44 | 120.2 | C26—C25—H25 | 119.7 |
C43—C44—H44 | 120.2 | C21—C26—C25 | 118.3 (3) |
C44—C45—C46 | 120.1 (3) | C21—C26—H26 | 120.8 |
C44—C45—H45 | 119.9 | C25—C26—H26 | 120.8 |
C46—C45—H45 | 119.9 | C36—C31—C32 | 121.1 (3) |
C41—C46—C45 | 120.7 (3) | C36—C31—O3 | 120.0 (2) |
C41—C46—H46 | 119.6 | C32—C31—O3 | 118.6 (2) |
C45—C46—H46 | 119.6 | C31—C32—C33 | 119.1 (3) |
O1—P1—O3 | 114.26 (11) | C31—C32—H32 | 120.5 |
O1—P1—O2 | 116.08 (11) | C33—C32—H32 | 120.5 |
O3—P1—O2 | 103.52 (11) | C34—C33—C32 | 121.2 (3) |
O1—P1—C2 | 114.70 (12) | C34—C33—H33 | 119.4 |
O3—P1—C2 | 103.79 (12) | C32—C33—H33 | 119.4 |
O2—P1—C2 | 102.91 (11) | C33—C34—C35 | 118.6 (3) |
C21—O2—P1 | 121.86 (17) | C33—C34—H34 | 120.7 |
C31—O3—P1 | 127.39 (17) | C35—C34—H34 | 120.7 |
C16—C11—C12 | 120.9 (3) | C34—C35—C36 | 121.3 (3) |
C16—C11—N1 | 120.9 (3) | C34—C35—H35 | 119.3 |
C12—C11—N1 | 118.2 (3) | C36—C35—H35 | 119.3 |
C11—C12—C13 | 118.7 (4) | C31—C36—C35 | 118.8 (3) |
C11—C12—H12 | 120.6 | C31—C36—H36 | 120.6 |
C13—C12—H12 | 120.6 | C35—C36—H36 | 120.6 |
C14—C13—C12 | 120.8 (4) | | |
| | | |
N2—C1—N1—C11 | 169.3 (3) | C1—N1—C11—C16 | 76.1 (4) |
S1—C1—N1—C11 | −10.3 (4) | C1—N1—C11—C12 | −106.3 (3) |
N1—C1—N2—C2 | −172.7 (3) | C16—C11—C12—C13 | 0.0 (5) |
S1—C1—N2—C2 | 6.9 (4) | N1—C11—C12—C13 | −177.5 (3) |
C1—N2—C2—C41 | −111.4 (3) | C11—C12—C13—C14 | 0.0 (6) |
C1—N2—C2—P1 | 119.1 (3) | C12—C13—C14—C15 | −0.4 (7) |
N2—C2—C41—C46 | −20.0 (4) | C13—C14—C15—C16 | 0.7 (6) |
P1—C2—C41—C46 | 103.6 (3) | C12—C11—C16—C15 | 0.2 (5) |
N2—C2—C41—C42 | 157.3 (3) | N1—C11—C16—C15 | 177.8 (3) |
P1—C2—C41—C42 | −79.2 (3) | C14—C15—C16—C11 | −0.6 (6) |
C46—C41—C42—C43 | 0.2 (5) | P1—O2—C21—C22 | 92.8 (3) |
C2—C41—C42—C43 | −177.1 (3) | P1—O2—C21—C26 | −90.3 (3) |
C41—C42—C43—C44 | −0.1 (5) | C26—C21—C22—C23 | −1.0 (5) |
C42—C43—C44—C45 | 0.3 (6) | O2—C21—C22—C23 | 175.8 (3) |
C43—C44—C45—C46 | −0.7 (6) | C21—C22—C23—C24 | 0.2 (6) |
C42—C41—C46—C45 | −0.6 (5) | C22—C23—C24—C25 | 0.3 (6) |
C2—C41—C46—C45 | 176.7 (3) | C23—C24—C25—C26 | −0.1 (6) |
C44—C45—C46—C41 | 0.8 (6) | C22—C21—C26—C25 | 1.2 (5) |
N2—C2—P1—O1 | 45.4 (2) | O2—C21—C26—C25 | −175.5 (3) |
C41—C2—P1—O1 | −82.7 (2) | C24—C25—C26—C21 | −0.6 (5) |
N2—C2—P1—O3 | −79.93 (19) | P1—O3—C31—C36 | −81.4 (3) |
C41—C2—P1—O3 | 151.9 (2) | P1—O3—C31—C32 | 104.7 (3) |
N2—C2—P1—O2 | 172.42 (17) | C36—C31—C32—C33 | −0.1 (5) |
C41—C2—P1—O2 | 44.3 (2) | O3—C31—C32—C33 | 173.7 (3) |
O1—P1—O2—C21 | −49.5 (3) | C31—C32—C33—C34 | 0.1 (5) |
O3—P1—O2—C21 | 76.6 (2) | C32—C33—C34—C35 | −0.3 (6) |
C2—P1—O2—C21 | −175.6 (2) | C33—C34—C35—C36 | 0.3 (6) |
O1—P1—O3—C31 | −9.7 (3) | C32—C31—C36—C35 | 0.1 (5) |
O2—P1—O3—C31 | −136.8 (2) | O3—C31—C36—C35 | −173.6 (3) |
C2—P1—O3—C31 | 116.0 (2) | C34—C35—C36—C31 | −0.3 (6) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.86 (2) | 1.98 (2) | 2.836 (3) | 170 (3) |
N2—H2···O1i | 0.84 (2) | 2.27 (3) | 3.033 (3) | 151 (3) |
Symmetry code: (i) −x, −y, −z. |
(III) diphenyl [2,2-dimethyl-1-(3-phenylthioureido)propyl]phosphonate
top
Crystal data top
C24H27N2O3PS | F(000) = 960 |
Mr = 454.51 | Dx = 1.256 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 10.688 (3) Å | θ = 22.7–28.8° |
b = 9.888 (2) Å | µ = 2.04 mm−1 |
c = 22.961 (2) Å | T = 293 K |
β = 97.790 (1)° | Prism, colourless |
V = 2404.2 (9) Å3 | 0.5 × 0.5 × 0.45 mm |
Z = 4 | |
Data collection top
AFC5S Rigaku diffractometer | 3100 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.015 |
Graphite monochromator | θmax = 67.5°, θmin = 3.9° |
ω scans | h = −12→12 |
Absorption correction: analytical (De Meulenaer & Tompa, 1965) | k = −8→11 |
Tmin = 0.427, Tmax = 0.464 | l = −27→27 |
4439 measured reflections | 3 standard reflections every 150 reflections |
4193 independent reflections | intensity decay: <2% |
Refinement top
Refinement on F2 | Secondary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.045 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.137 | w = 1/[σ2(Fo2) + (0.0821P)2 + 0.0698P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
4193 reflections | Δρmax = 0.22 e Å−3 |
289 parameters | Δρmin = −0.37 e Å−3 |
2 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0108 (6) |
Crystal data top
C24H27N2O3PS | V = 2404.2 (9) Å3 |
Mr = 454.51 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 10.688 (3) Å | µ = 2.04 mm−1 |
b = 9.888 (2) Å | T = 293 K |
c = 22.961 (2) Å | 0.5 × 0.5 × 0.45 mm |
β = 97.790 (1)° | |
Data collection top
AFC5S Rigaku diffractometer | 3100 reflections with I > 2σ(I) |
Absorption correction: analytical (De Meulenaer & Tompa, 1965) | Rint = 0.015 |
Tmin = 0.427, Tmax = 0.464 | 3 standard reflections every 150 reflections |
4439 measured reflections | intensity decay: <2% |
4193 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.045 | 2 restraints |
wR(F2) = 0.137 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.22 e Å−3 |
4193 reflections | Δρmin = −0.37 e Å−3 |
289 parameters | |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 0.17928 (6) | 0.49548 (6) | 0.62637 (3) | 0.0770 (2) | |
C1 | 0.3152 (2) | 0.5341 (2) | 0.60363 (8) | 0.0586 (5) | |
N1 | 0.3889 (2) | 0.6401 (2) | 0.62376 (8) | 0.0699 (5) | |
H1 | 0.4647 (12) | 0.642 (2) | 0.6158 (11) | 0.076 (8)* | |
N2 | 0.36643 (19) | 0.46038 (19) | 0.56292 (8) | 0.0651 (5) | |
H2 | 0.4402 (12) | 0.487 (2) | 0.5564 (9) | 0.061 (6)* | |
C2 | 0.3140 (2) | 0.3335 (2) | 0.53824 (9) | 0.0652 (6) | |
H201 | 0.2330 | 0.3200 | 0.5529 | 0.078* | |
C3 | 0.3976 (3) | 0.2084 (3) | 0.55747 (11) | 0.0802 (7) | |
C4 | 0.5148 (3) | 0.2015 (3) | 0.52621 (14) | 0.1040 (10) | |
H401 | 0.5676 | 0.1282 | 0.5421 | 0.156* | |
H402 | 0.5607 | 0.2850 | 0.5320 | 0.156* | |
H403 | 0.4896 | 0.1871 | 0.4849 | 0.156* | |
C5 | 0.4382 (4) | 0.2178 (3) | 0.62412 (14) | 0.1215 (13) | |
H501 | 0.4934 | 0.2939 | 0.6326 | 0.182* | |
H502 | 0.4817 | 0.1365 | 0.6378 | 0.182* | |
H503 | 0.3649 | 0.2289 | 0.6436 | 0.182* | |
C6 | 0.3178 (3) | 0.0799 (3) | 0.54434 (16) | 0.1045 (10) | |
H601 | 0.2403 | 0.0886 | 0.5609 | 0.157* | |
H602 | 0.3639 | 0.0030 | 0.5614 | 0.157* | |
H603 | 0.2992 | 0.0677 | 0.5026 | 0.157* | |
P1 | 0.27923 (6) | 0.37191 (6) | 0.46068 (2) | 0.0621 (2) | |
O1 | 0.38380 (14) | 0.42621 (17) | 0.43252 (7) | 0.0715 (4) | |
O2 | 0.22051 (16) | 0.23709 (15) | 0.43225 (7) | 0.0731 (4) | |
O3 | 0.16046 (15) | 0.46780 (15) | 0.45700 (7) | 0.0702 (4) | |
C11 | 0.3580 (2) | 0.7455 (2) | 0.66184 (10) | 0.0673 (6) | |
C12 | 0.2480 (3) | 0.8163 (3) | 0.65081 (14) | 0.0951 (9) | |
H12 | 0.1889 | 0.7936 | 0.6187 | 0.114* | |
C13 | 0.2240 (4) | 0.9214 (3) | 0.68708 (19) | 0.1168 (12) | |
H13 | 0.1477 | 0.9676 | 0.6797 | 0.140* | |
C14 | 0.3091 (4) | 0.9587 (3) | 0.73316 (16) | 0.1100 (11) | |
H14 | 0.2914 | 1.0293 | 0.7575 | 0.132* | |
C15 | 0.4209 (4) | 0.8918 (3) | 0.74348 (14) | 0.1235 (13) | |
H15 | 0.4812 | 0.9180 | 0.7745 | 0.148* | |
C16 | 0.4456 (3) | 0.7832 (3) | 0.70750 (12) | 0.1001 (9) | |
H16 | 0.5218 | 0.7369 | 0.7149 | 0.120* | |
C21 | 0.1867 (3) | 0.2258 (2) | 0.37060 (10) | 0.0705 (6) | |
C22 | 0.2550 (3) | 0.1430 (3) | 0.34030 (12) | 0.0946 (9) | |
H22 | 0.3255 | 0.0976 | 0.3590 | 0.114* | |
C23 | 0.2165 (4) | 0.1276 (4) | 0.27988 (15) | 0.1134 (11) | |
H23 | 0.2622 | 0.0714 | 0.2581 | 0.136* | |
C24 | 0.1141 (4) | 0.1932 (4) | 0.25290 (14) | 0.1096 (10) | |
H24 | 0.0899 | 0.1826 | 0.2127 | 0.132* | |
C25 | 0.0467 (3) | 0.2742 (4) | 0.28439 (14) | 0.1132 (11) | |
H25 | −0.0239 | 0.3192 | 0.2657 | 0.136* | |
C26 | 0.0816 (3) | 0.2909 (3) | 0.34405 (12) | 0.0950 (9) | |
H26 | 0.0343 | 0.3456 | 0.3658 | 0.114* | |
C31 | 0.1481 (2) | 0.6040 (2) | 0.44149 (11) | 0.0689 (6) | |
C32 | 0.1780 (3) | 0.6484 (3) | 0.38863 (13) | 0.0936 (9) | |
H32 | 0.2129 | 0.5903 | 0.3633 | 0.112* | |
C33 | 0.1541 (4) | 0.7841 (4) | 0.37403 (18) | 0.1240 (14) | |
H33 | 0.1737 | 0.8187 | 0.3387 | 0.149* | |
C34 | 0.1005 (4) | 0.8666 (4) | 0.4132 (3) | 0.1406 (17) | |
H34 | 0.0838 | 0.9567 | 0.4035 | 0.169* | |
C35 | 0.0724 (4) | 0.8185 (4) | 0.4650 (2) | 0.1260 (13) | |
H35 | 0.0380 | 0.8757 | 0.4907 | 0.151* | |
C36 | 0.0946 (3) | 0.6854 (3) | 0.47959 (13) | 0.0883 (8) | |
H36 | 0.0736 | 0.6510 | 0.5147 | 0.106* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0839 (5) | 0.0743 (4) | 0.0793 (4) | −0.0083 (3) | 0.0346 (3) | −0.0059 (3) |
C1 | 0.0676 (13) | 0.0567 (11) | 0.0533 (11) | 0.0027 (10) | 0.0144 (9) | −0.0011 (9) |
N1 | 0.0722 (13) | 0.0682 (12) | 0.0736 (12) | −0.0074 (10) | 0.0252 (10) | −0.0187 (9) |
N2 | 0.0685 (12) | 0.0645 (11) | 0.0650 (11) | −0.0105 (9) | 0.0194 (9) | −0.0140 (9) |
C2 | 0.0771 (14) | 0.0553 (12) | 0.0656 (13) | −0.0041 (11) | 0.0185 (11) | −0.0098 (10) |
C3 | 0.0995 (19) | 0.0645 (14) | 0.0756 (15) | 0.0098 (14) | 0.0079 (13) | −0.0048 (12) |
C4 | 0.097 (2) | 0.092 (2) | 0.121 (2) | 0.0274 (18) | 0.0086 (18) | −0.0111 (18) |
C5 | 0.169 (3) | 0.103 (2) | 0.0840 (19) | 0.035 (2) | −0.012 (2) | 0.0042 (18) |
C6 | 0.132 (3) | 0.0607 (15) | 0.121 (2) | 0.0038 (17) | 0.018 (2) | 0.0073 (15) |
P1 | 0.0689 (4) | 0.0570 (3) | 0.0622 (3) | −0.0041 (3) | 0.0156 (3) | −0.0081 (2) |
O1 | 0.0700 (10) | 0.0784 (10) | 0.0697 (9) | −0.0079 (8) | 0.0229 (8) | −0.0067 (8) |
O2 | 0.0911 (11) | 0.0609 (9) | 0.0673 (9) | −0.0085 (8) | 0.0115 (8) | −0.0124 (7) |
O3 | 0.0711 (10) | 0.0563 (8) | 0.0865 (10) | 0.0016 (7) | 0.0220 (8) | 0.0029 (7) |
C11 | 0.0885 (16) | 0.0573 (12) | 0.0592 (12) | −0.0021 (12) | 0.0208 (11) | −0.0064 (9) |
C12 | 0.096 (2) | 0.0744 (16) | 0.114 (2) | 0.0073 (16) | 0.0114 (17) | −0.0185 (15) |
C13 | 0.111 (3) | 0.080 (2) | 0.164 (4) | 0.0141 (19) | 0.035 (2) | −0.030 (2) |
C14 | 0.163 (3) | 0.0755 (18) | 0.101 (2) | 0.010 (2) | 0.051 (2) | −0.0159 (17) |
C15 | 0.191 (4) | 0.094 (2) | 0.0776 (19) | 0.014 (3) | −0.010 (2) | −0.0262 (16) |
C16 | 0.126 (2) | 0.0842 (18) | 0.0835 (18) | 0.0202 (18) | −0.0085 (17) | −0.0219 (15) |
C21 | 0.0836 (16) | 0.0635 (13) | 0.0657 (13) | −0.0082 (12) | 0.0146 (12) | −0.0148 (11) |
C22 | 0.111 (2) | 0.0879 (19) | 0.0840 (18) | 0.0190 (17) | 0.0109 (16) | −0.0212 (15) |
C23 | 0.136 (3) | 0.117 (3) | 0.088 (2) | 0.024 (2) | 0.020 (2) | −0.0365 (19) |
C24 | 0.118 (3) | 0.128 (3) | 0.0808 (19) | 0.000 (2) | 0.0068 (18) | −0.0278 (19) |
C25 | 0.103 (2) | 0.138 (3) | 0.092 (2) | 0.016 (2) | −0.0092 (17) | −0.031 (2) |
C26 | 0.0858 (18) | 0.114 (2) | 0.0839 (17) | 0.0072 (17) | 0.0059 (14) | −0.0325 (17) |
C31 | 0.0689 (14) | 0.0594 (13) | 0.0754 (15) | −0.0075 (11) | −0.0011 (11) | 0.0026 (11) |
C32 | 0.100 (2) | 0.093 (2) | 0.0843 (17) | −0.0124 (17) | 0.0016 (15) | 0.0190 (15) |
C33 | 0.124 (3) | 0.117 (3) | 0.121 (3) | −0.028 (2) | −0.020 (2) | 0.050 (2) |
C34 | 0.126 (3) | 0.080 (2) | 0.202 (5) | −0.002 (2) | −0.028 (3) | 0.039 (3) |
C35 | 0.129 (3) | 0.0659 (18) | 0.180 (4) | 0.013 (2) | 0.008 (3) | −0.007 (2) |
C36 | 0.0911 (19) | 0.0656 (15) | 0.108 (2) | 0.0069 (14) | 0.0146 (15) | −0.0118 (14) |
Geometric parameters (Å, º) top
S1—C1 | 1.654 (2) | C12—H12 | 0.9300 |
C1—N1 | 1.354 (3) | C13—C14 | 1.350 (5) |
C1—N2 | 1.358 (3) | C13—H13 | 0.9300 |
N1—C11 | 1.427 (3) | C14—C15 | 1.359 (5) |
N1—H1 | 0.854 (10) | C14—H14 | 0.9300 |
N2—C2 | 1.457 (3) | C15—C16 | 1.401 (4) |
N2—H2 | 0.864 (10) | C15—H15 | 0.9300 |
C2—C3 | 1.554 (3) | C16—H16 | 0.9300 |
C2—P1 | 1.809 (2) | C21—C22 | 1.350 (3) |
C2—H201 | 0.9800 | C21—C26 | 1.365 (4) |
C3—C4 | 1.527 (4) | C22—C23 | 1.401 (4) |
C3—C5 | 1.536 (4) | C22—H22 | 0.9300 |
C3—C6 | 1.538 (4) | C23—C24 | 1.348 (5) |
C4—H401 | 0.9600 | C23—H23 | 0.9300 |
C4—H402 | 0.9600 | C24—C25 | 1.350 (4) |
C4—H403 | 0.9600 | C24—H24 | 0.9300 |
C5—H501 | 0.9600 | C25—C26 | 1.380 (4) |
C5—H502 | 0.9600 | C25—H25 | 0.9300 |
C5—H503 | 0.9600 | C26—H26 | 0.9300 |
C6—H601 | 0.9600 | C31—C32 | 1.368 (3) |
C6—H602 | 0.9600 | C31—C36 | 1.370 (3) |
C6—H603 | 0.9600 | C32—C33 | 1.398 (5) |
P1—O1 | 1.4668 (15) | C32—H32 | 0.9300 |
P1—O2 | 1.5768 (15) | C33—C34 | 1.394 (6) |
P1—O3 | 1.5774 (16) | C33—H33 | 0.9300 |
O2—C21 | 1.417 (3) | C34—C35 | 1.352 (6) |
O3—C31 | 1.395 (3) | C34—H34 | 0.9300 |
C11—C16 | 1.359 (4) | C35—C36 | 1.371 (4) |
C11—C12 | 1.362 (4) | C35—H35 | 0.9300 |
C12—C13 | 1.378 (4) | C36—H36 | 0.9300 |
| | | |
N1—C1—N2 | 112.37 (19) | C11—C12—H12 | 119.9 |
N1—C1—S1 | 124.48 (16) | C13—C12—H12 | 119.9 |
N2—C1—S1 | 123.14 (17) | C14—C13—C12 | 121.3 (3) |
C1—N1—C11 | 127.0 (2) | C14—C13—H13 | 119.4 |
C1—N1—H1 | 117.9 (17) | C12—C13—H13 | 119.4 |
C11—N1—H1 | 114.8 (17) | C13—C14—C15 | 119.1 (3) |
C1—N2—C2 | 124.09 (19) | C13—C14—H14 | 120.4 |
C1—N2—H2 | 114.6 (15) | C15—C14—H14 | 120.4 |
C2—N2—H2 | 120.7 (15) | C14—C15—C16 | 120.1 (3) |
N2—C2—C3 | 113.50 (19) | C14—C15—H15 | 120.0 |
N2—C2—P1 | 102.66 (15) | C16—C15—H15 | 120.0 |
C3—C2—P1 | 118.69 (15) | C11—C16—C15 | 120.0 (3) |
N2—C2—H201 | 107.1 | C11—C16—H16 | 120.0 |
C3—C2—H201 | 107.1 | C15—C16—H16 | 120.0 |
P1—C2—H201 | 107.1 | C22—C21—C26 | 121.7 (3) |
C4—C3—C5 | 109.4 (3) | C22—C21—O2 | 118.7 (2) |
C4—C3—C6 | 109.9 (2) | C26—C21—O2 | 119.5 (2) |
C5—C3—C6 | 108.6 (3) | C21—C22—C23 | 118.0 (3) |
C4—C3—C2 | 112.2 (2) | C21—C22—H22 | 121.0 |
C5—C3—C2 | 108.0 (2) | C23—C22—H22 | 121.0 |
C6—C3—C2 | 108.6 (2) | C24—C23—C22 | 120.9 (3) |
C3—C4—H401 | 109.5 | C24—C23—H23 | 119.5 |
C3—C4—H402 | 109.5 | C22—C23—H23 | 119.5 |
H401—C4—H402 | 109.5 | C23—C24—C25 | 119.8 (3) |
C3—C4—H403 | 109.5 | C23—C24—H24 | 120.1 |
H401—C4—H403 | 109.5 | C25—C24—H24 | 120.1 |
H402—C4—H403 | 109.5 | C24—C25—C26 | 120.7 (3) |
C3—C5—H501 | 109.5 | C24—C25—H25 | 119.6 |
C3—C5—H502 | 109.5 | C26—C25—H25 | 119.6 |
H501—C5—H502 | 109.5 | C21—C26—C25 | 118.8 (3) |
C3—C5—H503 | 109.5 | C21—C26—H26 | 120.6 |
H501—C5—H503 | 109.5 | C25—C26—H26 | 120.6 |
H502—C5—H503 | 109.5 | C32—C31—C36 | 123.1 (3) |
C3—C6—H601 | 109.5 | C32—C31—O3 | 120.7 (2) |
C3—C6—H602 | 109.5 | C36—C31—O3 | 116.0 (2) |
H601—C6—H602 | 109.5 | C31—C32—C33 | 117.6 (3) |
C3—C6—H603 | 109.5 | C31—C32—H32 | 121.2 |
H601—C6—H603 | 109.5 | C33—C32—H32 | 121.2 |
H602—C6—H603 | 109.5 | C34—C33—C32 | 119.0 (4) |
O1—P1—O2 | 114.28 (9) | C34—C33—H33 | 120.5 |
O1—P1—O3 | 114.33 (9) | C32—C33—H33 | 120.5 |
O2—P1—O3 | 102.34 (9) | C35—C34—C33 | 121.4 (4) |
O1—P1—C2 | 116.32 (11) | C35—C34—H34 | 119.3 |
O2—P1—C2 | 104.31 (9) | C33—C34—H34 | 119.3 |
O3—P1—C2 | 103.62 (10) | C34—C35—C36 | 120.1 (4) |
C21—O2—P1 | 120.91 (14) | C34—C35—H35 | 119.9 |
C31—O3—P1 | 129.93 (15) | C36—C35—H35 | 119.9 |
C16—C11—C12 | 119.3 (2) | C31—C36—C35 | 118.7 (3) |
C16—C11—N1 | 118.7 (2) | C31—C36—H36 | 120.6 |
C12—C11—N1 | 121.8 (2) | C35—C36—H36 | 120.6 |
C11—C12—C13 | 120.1 (3) | | |
| | | |
N2—C1—N1—C11 | 173.0 (2) | N1—C11—C12—C13 | −177.0 (3) |
S1—C1—N1—C11 | −8.1 (3) | C11—C12—C13—C14 | 1.5 (5) |
N1—C1—N2—C2 | 173.6 (2) | C12—C13—C14—C15 | 0.6 (6) |
S1—C1—N2—C2 | −5.3 (3) | C13—C14—C15—C16 | −1.7 (6) |
C1—N2—C2—C3 | −111.5 (3) | C12—C11—C16—C15 | 1.5 (5) |
C1—N2—C2—P1 | 119.2 (2) | N1—C11—C16—C15 | 176.1 (3) |
N2—C2—C3—C4 | −74.6 (3) | C14—C15—C16—C11 | 0.6 (5) |
P1—C2—C3—C4 | 46.1 (3) | P1—O2—C21—C22 | 110.7 (2) |
N2—C2—C3—C5 | 46.1 (3) | P1—O2—C21—C26 | −73.7 (3) |
P1—C2—C3—C5 | 166.8 (2) | C26—C21—C22—C23 | 1.4 (5) |
N2—C2—C3—C6 | 163.8 (2) | O2—C21—C22—C23 | 176.8 (3) |
P1—C2—C3—C6 | −75.6 (3) | C21—C22—C23—C24 | −0.2 (5) |
N2—C2—P1—O1 | 53.79 (18) | C22—C23—C24—C25 | −0.5 (6) |
C3—C2—P1—O1 | −72.3 (2) | C23—C24—C25—C26 | 0.1 (6) |
N2—C2—P1—O2 | −179.35 (14) | C22—C21—C26—C25 | −1.8 (5) |
C3—C2—P1—O2 | 54.6 (2) | O2—C21—C26—C25 | −177.2 (3) |
N2—C2—P1—O3 | −72.57 (16) | C24—C25—C26—C21 | 1.1 (5) |
C3—C2—P1—O3 | 161.37 (18) | P1—O3—C31—C32 | 55.8 (3) |
O1—P1—O2—C21 | −48.7 (2) | P1—O3—C31—C36 | −129.7 (2) |
O3—P1—O2—C21 | 75.47 (19) | C36—C31—C32—C33 | 1.2 (4) |
C2—P1—O2—C21 | −176.79 (18) | O3—C31—C32—C33 | 175.2 (3) |
O1—P1—O3—C31 | −13.7 (2) | C31—C32—C33—C34 | −0.6 (5) |
O2—P1—O3—C31 | −137.80 (19) | C32—C33—C34—C35 | 0.6 (6) |
C2—P1—O3—C31 | 113.9 (2) | C33—C34—C35—C36 | −1.1 (6) |
C1—N1—C11—C16 | 134.8 (3) | C32—C31—C36—C35 | −1.6 (4) |
C1—N1—C11—C12 | −50.7 (4) | O3—C31—C36—C35 | −175.9 (3) |
C16—C11—C12—C13 | −2.6 (5) | C34—C35—C36—C31 | 1.5 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.85 (1) | 2.19 (2) | 2.976 (3) | 153 (1) |
N2—H2···O1i | 0.86 (1) | 2.05 (1) | 2.884 (3) | 162 (1) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Experimental details
| (I) | (II) | (III) |
Crystal data |
Chemical formula | C28H27N2O3PS | C26H23N2O3PS | C24H27N2O3PS |
Mr | 502.55 | 474.49 | 454.51 |
Crystal system, space group | Triclinic, P1 | Triclinic, P1 | Monoclinic, P21/c |
Temperature (K) | 293 | 293 | 293 |
a, b, c (Å) | 9.951 (1), 12.201 (1), 11.844 (1) | 9.953 (1), 10.046 (1), 12.701 (1) | 10.688 (3), 9.888 (2), 22.961 (2) |
α, β, γ (°) | 100.40 (1), 102.90 (1), 102.90 (1) | 96.66 (1), 104.45 (1), 99.84 (1) | 90, 97.790 (1), 90 |
V (Å3) | 1325.6 (2) | 1194.8 (2) | 2404.2 (9) |
Z | 2 | 2 | 4 |
Radiation type | Cu Kα | Cu Kα | Cu Kα |
µ (mm−1) | 1.91 | 2.09 | 2.04 |
Crystal size (mm) | 0.50 × 0.30 × 0.20 | 0.2 × 0.2 × 0.1 | 0.5 × 0.5 × 0.45 |
|
Data collection |
Diffractometer | AFC5S Rigaku diffractometer | AFC5S Rigaku diffractometer | AFC5S Rigaku diffractometer |
Absorption correction | Analytical (De Meulenaer & Tompa, 1965) | Analytical (De Meulenaer & Tompa, 1965) | Analytical (De Meulenaer & Tompa, 1965) |
Tmin, Tmax | 0.448, 0.701 | 0.675, 0.836 | 0.427, 0.464 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4878, 4637, 3089 | 4431, 4169, 2147 | 4439, 4193, 3100 |
Rint | 0.030 | 0.019 | 0.015 |
(sin θ/λ)max (Å−1) | 0.599 | 0.599 | 0.599 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.119, 0.94 | 0.038, 0.090, 1.00 | 0.045, 0.137, 1.06 |
No. of reflections | 4637 | 4169 | 4193 |
No. of parameters | 325 | 307 | 289 |
No. of restraints | 8 | 8 | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.21, −0.28 | 0.19, −0.23 | 0.22, −0.37 |
Selected geometric parameters (Å, º) for (I) topS1—C1 | 1.663 (2) | C2—P1 | 1.799 (2) |
C1—N1 | 1.349 (3) | P1—O1 | 1.4680 (15) |
C1—N2 | 1.363 (3) | P1—O3 | 1.5691 (17) |
N1—C11 | 1.434 (3) | P1—O2 | 1.5740 (16) |
N2—C2 | 1.457 (3) | | |
| | | |
N1—C1—N2 | 112.47 (19) | O1—P1—O2 | 115.74 (9) |
N1—C1—S1 | 124.00 (17) | O3—P1—O2 | 103.91 (10) |
N2—C1—S1 | 123.53 (17) | O1—P1—C2 | 114.59 (10) |
C1—N2—C2 | 124.18 (19) | O3—P1—C2 | 105.48 (10) |
O1—P1—O3 | 114.03 (9) | O2—P1—C2 | 101.63 (9) |
| | | |
S1—C1—N1—C11 | −4.5 (4) | S1—C1—N2—C2 | 9.0 (3) |
Hydrogen-bond geometry (Å, º) for (I) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.82 (2) | 2.06 (2) | 2.861 (2) | 163 (2) |
N2—H2···O1i | 0.89 (2) | 2.14 (2) | 2.967 (2) | 153 (2) |
Symmetry code: (i) −x, −y, −z. |
Selected geometric parameters (Å, º) for (II) topS1—C1 | 1.662 (3) | C2—P1 | 1.806 (3) |
C1—N1 | 1.349 (3) | P1—O1 | 1.4677 (19) |
C1—N2 | 1.352 (3) | P1—O3 | 1.5680 (19) |
N2—C2 | 1.456 (3) | P1—O2 | 1.5757 (18) |
| | | |
N1—C1—N2 | 112.7 (2) | O1—P1—O2 | 116.08 (11) |
N1—C1—S1 | 123.7 (2) | O3—P1—O2 | 103.52 (11) |
N2—C1—S1 | 123.5 (2) | O1—P1—C2 | 114.70 (12) |
C1—N2—C2 | 124.2 (3) | O3—P1—C2 | 103.79 (12) |
O1—P1—O3 | 114.26 (11) | O2—P1—C2 | 102.91 (11) |
Hydrogen-bond geometry (Å, º) for (II) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.86 (2) | 1.98 (2) | 2.836 (3) | 170 (3) |
N2—H2···O1i | 0.84 (2) | 2.27 (3) | 3.033 (3) | 151 (3) |
Symmetry code: (i) −x, −y, −z. |
Selected geometric parameters (Å, º) for (III) topS1—C1 | 1.654 (2) | C1—N2 | 1.358 (3) |
C1—N1 | 1.354 (3) | N2—C2 | 1.457 (3) |
| | | |
N1—C1—N2 | 112.37 (19) | O1—P1—O3 | 114.33 (9) |
N1—C1—S1 | 124.48 (16) | O2—P1—O3 | 102.34 (9) |
N2—C1—S1 | 123.14 (17) | O1—P1—C2 | 116.32 (11) |
C1—N2—C2 | 124.09 (19) | O2—P1—C2 | 104.31 (9) |
O1—P1—O2 | 114.28 (9) | O3—P1—C2 | 103.62 (10) |
Hydrogen-bond geometry (Å, º) for (III) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.85 (1) | 2.19 (2) | 2.976 (3) | 153 (1) |
N2—H2···O1i | 0.86 (1) | 2.05 (1) | 2.884 (3) | 162 (1) |
Symmetry code: (i) −x+1, −y+1, −z+1. |